


Dream Lover

by LightLeadingMe



Category: Will & Grace
Genre: Confessions, Dream Sex, F/M, Friendship, Wet Dream
Language: English
Status: Completed
Published: 2018-08-14
Updated: 2018-11-12
Packaged: 2019-06-27 02:43:53
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 2
Words: 3,057
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15676413
Author URL: https://archiveofourown.org/users/LightLeadingMe/pseuds/LightLeadingMe
Summary: An inquisitive question about sex dreams reveals a little too much between Jack and Karen.





	1. Chapter 1

"What's your dirtiest sex dream?"

He contemplated the question for a long moment, his heart rate speeding up significantly as the memory of one of his sex dreams sprang to mind.

"Um, well..." he cleared his throat and avoided her curious eyes, his fingers twisting together nervously in his lap. "I'm, um, tied up and my, er, partner is straddling me... and we're, ya know, doing it..."

She hummed, nodding her head at him. "Who's the guy," she asked. At his confused expression she elaborated with a roll of her eyes. "In the dream?"

"Oh!" he waved her off and looked back down at his lap with a shrug. Should he be completely honest? Would it freak her out? "Have you ever had a sex dream about a friend?"

Karen looked surprised by the question, but she nodded anyway. "Well, yeah, plenty of times. But what does that have to do with-" she gasped at the sudden realization and Jack winced. "Will?!"

 

Jack reared back as if she just struck him across the face. "Ew! No, not Will!" he shrieked, offended she would even go there.

Karen continued to smile, her eyes filled with curiosity. "Well, it can't be Grace..." 

Jack kept his eyes on his lap for several seconds, but at her complete silence, he raised his head to catch her wide eyed expression. He couldn't really read her at that moment, it seemed like a mixture of emotions were constantly crossing her face and he was unable to identify any of them. 

" _Me_?" 

With a sigh, Jack answered her question on a shrug and a bite of his lip. "I'm just as surprised as you are," he told her, sounding exasperated. "And it always starts with you tying me up-"

"Wait a minute, wait a minute," she interrupted him, shifting on the couch as if the new position would help her understand him better. " _Always_?" Jack winced, realizing what he just admitted. "It's a recurring dream?"

Jack felt his face flush and he gulped loudly. "Yeah."

Karen's eyebrows shot up into her hairline and her mouth hung open almost comically. She stared him dead in the face and Jack did everything to avoid her gaze, feeling vulnerable under the scrutiny. It was several minutes of uncomfortable silence before Karen seemed to gather herself after her initial shock. She cleared her throat and crossed her legs on the couch, her knee touching his. "So you said it starts with me tying you up?"

Jack knew she would never stop bothering him until he described the vivid dream so with a regretful sound of annoyance, he took in a deep breath and began to explain. "It's always late at night, the moon is shining through the window and I wake up to feel someone... well, you... pulling my arms above my head and tying my wrists to the headboard...."

* * *

_The room was dark, the moon casting a perfect illumination on his naked body. His muscles twitched and stretched as began to rouse from his slumber. A small frown covered his perfectly pouty lips and his brows furrowed as he felt his arms being raised above his head. He fluttered his eyes open just in time to see her above him, her fingers deftly tying his wrists to the metal headboard. His frown deepened and he tugged on the restraints, catching the smirk on her face in the shadows. He opened his mouth to question her, but she anticipated his inquisitiveness and placed her finger over his lips, shushing him. As she crawled away from the headboard and toward the middle of the bed into the moonlight, he realized she was stark naked as well, her pale, soft flesh almost glowing. He tensed up, wanting to reach out to touch her, but being unable to._

_She giggled, noticing his frustration. She straddled his waist, her thighs lightly squeezing him, and she planted each hand on the pillow that his head was resting on, her long hair cascading perfectly over her shoulders and ticking his neck. Her mouth hovered just over his, her eyes filled with lust and passion. He waited for her to kiss him, but she never did. Taking matters into his own hands, he raised his head up to capture her lips, but she moved back at the last second, a reprimanding look in her eye. She sat back on him and he groaned when he felt her heated core on his abs. She smiled down at him teasingly and reached behind her, her eyes never leaving his wanting face, grabbing his already stiff cock in her hand. He gasped when she began to stroke him leisurely, occasionally smoothing her hand lower to cup his balls before grabbing his shaft again and pumping up and down._

_She watched his face, her bottom lip caught between her teeth and her eyes slightly hooded. She was a goddess._

_He involuntarily bucked up when she squeezed the head and immediately she took her hand away, making him let out a strained whimper. She ghosted her nails down his chest, grinning as she watched the goosebumps rise on his skin. She leaned over and covered his nipple with her mouth, her tongue flicking over it until it hardened. She looked up and locked her eyes on his before she took the bud in her mouth and suckled gently. He shivered and once again pulled at his restraints, feeling the burning in wrists and the tingling in his arms. She raked her nails against his abs, lightly digging in when she reached his groin and then dragged them back up again to his chest. She licked his nipple one last time and then sat back up, arching her back to give him a beautiful view of her large breasts. Her own nipples were hard and begging for his touch and he could feel the moisture and heat radiating from between her legs on his abdomen. As if reading his mind, she moved her hands slowly up her body to her chest, grasping her breasts in her hands. She twisted her nipples between her fingers and massaged the glorious mounds, her hips rocking back and forth over his stomach._

_"Please," he whispered, his voice trembling with need._

_It was the first either of them spoke and she paused her movements, her gaze unreadable. She placed her hands on his pecs and shifted her hips back a bit so he was perfectly lined up with her entrance. She felt his tip bump her clit and she took in a sharp breath before she lowered her hips, feeling him enter her slowly. He grunted, scrunching his face up as she sat down on him until he was fully buried in her, their hips completely connected. She raised her hips up tantalizingly slow, making sure she felt every inch of him as she went, clenching around him as she reached the top, and then slammed back down. They groaned together, her head tossed back and his eyes tightly shut. She continued at a slow pace for a few minutes, reveling in the sound their bodies made when they slapped together._

_She looked down on him as she saw the muscles in his arms bulging as he gripped the headboard and she increased her pace, her breasts bouncing as she rode him. He assisted by thrusting up and they felt themselves nearing the edge quickly. Moans, sighs, and gasps filled the room until finally a shriek and cry echoed as they reached their peak together._

_"Oh! Jack!"_

_"Karen!"_

* * *

 "...And then I wake up." 

Karen sat dumbfounded, staring at Jack blankly as he finished his telling of the dream. She had no idea what to say to him and she noticed Jack looked just as conflicted.

He watched her for a few moments, waiting impatiently and uncomfortably for her to say something, anything. He wiped his sweaty palms on his pants and bit his lip with a shrug. "I freaked you out, didn't I? Damn it!" he sighed, smacking a hand to his forehead. "Look, forget I said anything, okay? Please?"

Karen shook her head and gulped audibly, straightening her posture a bit as she rapidly blinked. "I, uh, wow, Poodle..." She raised a hand up and began to fan herself, her cheeks pink from blushing. "That is _hot_."

Jack didn't know how to respond. In all honestly, it was really hot. He more often than not woke up with a boner, sometimes to cum soaked sheets even, but he didn't want to tell her that. Admitting that he had sex dreams about girls was already a little too much. Well, sex dreams about Karen. If he was having sex dreams about _women_ he would be admitting himself into the psychiatric ward immediately. Point being, he didn't want to scare off his best friend even more than what he probably already did. 

"I mean, _damn_ ," she stood up and grabbed her purse. "I've had some pretty good sex dreams in my day, but whoo! That was _good_..."

Jack followed her out the door and to the elevator. "Where are you going?" 

"I'm going home, honey. I gotta fuck Stan after hearing about that dream of yours!" She pushed the elevator button and continued to fan herself as she repeated some of the things he told her in her head. She winced when she felt her arousal between her legs and took the hand she was using as a fan and placed it on the wall, leaning as she breathed, trying to calm her fast beating heart.

"Wait," Jack spoke up, confusion covering his features. "So we're okay? You're not freaked out that I've had dreams about you?"

The elevator dinged and she pushed herself off the wall with a scoff before she entered, giving him an incredulous look. "No, honey! I've had dreams about you. Hell, I've had dreams about Grace!"

Jack gawked. "Really?"

Karen nodded and whistled. "That girl is _nasty_ in my dreams..."

He shook his head, grimacing at the image and waved his hands in front of himself in disgust. "Ew, no. I mean, you've had dreams about me too?"

Her gaze turned flirty, almost seductive, and she licked her lips with a smirk. "I'll tell you about them one day."

The doors slid closed and Jack stood there, his eyes fixated on the elevator, his mind racing and his heart pounding as he imagined the dreams Karen was having about him. 


	2. Chapter 2

**Notes for the Chapter:**

> I was bribed to write this and I regret nothing.

A commercial came on and Karen leaned over to grab her martini when Jack clicked the power button on the remote and the room suddenly was enraptured in darkness. Karen turned her head to look at him as she took a sip from the glass and raised her eyebrow at the serious expression on his face. "Something on your mind, honey?"

Jack licked his dry lips, his heart racing in his chest. "Y-ya know a while ago when I told you about my-uh, sex dreams?"

Grinning, Karen set the martini back on the table and sat back against the cushions of the small couch. "Yes, I remember." She tilted her head at him, noticing his nervous posture. "Did you have another one? Or is it the same-"

"No," he interrupted, waving his hands in front of him as he shook his head. "I just... You told me that you had dreams about me too and that you would tell me about them one day and I was just wondering..."

Karen let out a short laugh. "I see," she nodded and pulled her knees up underneath her, getting more comfortable on the sofa. "You're sure you want me to tell you? I know all that hetero talk freaks you out."

Sighing, Jack nodded. "Please," he said, putting his hand on her knee. "I'm hoping once you tell me what kind of dreams you're having that my mind will miraculously stop imagining it."

With a smirk, Karen cleared her throat, silently wracking her brain for the memory of her dreams. "Well, you're very dominant in my dreams. Very masculine and demanding..."

* * *

_A whimper escaped her throat as he delivered another blow to her ass cheek, the skin there a deep red and marked with hand prints. His large hand massaged her flesh and then he smacked her again, this time causing her to cry out in the mixture of pain and pleasure. At the sound, he grabbed her around her waist and threw her down onto the mattress, her body bouncing slightly from the springs. His body loomed over her as he sat on his knees and she shivered, knowing she was about to be punished for making a sound._

_"Now now, Karen," he spoke, his voice rough and deep with arousal. "I told you that you are only allowed to speak when I give you permission." He looked down at her with disapproval, but she could see the amusement and lust lurking just beneath the surface of his gaze. The whirring of the vibrator made her bite her lip and when it was placed in the most perfect position on her clit, it took everything in her to not scream. "Are you going to be quiet until I say?" he asked, pushing the device even harder against her. An orgasm was just out of reach, but she knew she was not allowed to come yet so she just bit down on her lip and nodded her head quickly. He rubbed the vibrator against her a few more times for good measure and then turned it off, setting it aside. "Good girl."_

_Her breaths were coming out more like pants, her body flushed and her pussy throbbing with need for release. He kicked his legs back behind him and stood up at the end of the bed, his hands grabbing her by the ankles so he could pull her down to him. She gasped when his cock brushed against her sensitive button and stared up into his blue eyes adoringly, her hands gripping the sheets in anticipation. He smoothed his hands along her calves and down to her thighs, parting them as far he pleased. He told her to keep them spread and waited until she nodded at him before he thrust himself inside of her. Her hand flew to her mouth to stifle the sound that nearly escaped, her muscles contracting at just the feeling of him filling her up. He smirked down at her, his hands placed on the inside of her thighs, fingers hooked around her hips so that he could push in and out of her rapidly, the position giving him leverage._

_The sounds their bodies made as they slapped together echoed in the room, a raunchy, exotic sound that only increased their pleasure. He gazed down at her, seeing the whites of her eyes as they rolled back and the redness of her face, knowing she was trying so hard to hold back from her release. He let out a groan himself, the sight almost enough to make him come, but he too held back, wanting her to have hers first. He raised a hand from her leg and grabbed her wrist to pull her hand off her mouth as he leaned down over her, the movements of his hips never ceasing. The angle hit a new depth and he waited until her eyes popped open as he grinned._

_"Now."_

_He was sure the windows would shatter at the loud screams that emitted from her throat. She clenched down so hard on him that she almost pushed him out, but he powered through and continued his thrusts until he came as well. Her back was arched so far off the bed, he wasn't even sure her shoulders were touching the sheets anymore, but he didn't stop even as she thrashed about, until she came again. This time he pulled out of her and stepped back on wobbly legs to see her body convulse in a wrath of pleasure, her knees clapping together as she curled onto her side and sobbed. He breathed heavily, the exertion tiring him, and he moved to climb back onto the bed beside her, smirking when he noticed the drenched sheets near the end of the bed._

_It took a while for her to calm down enough to roll onto her back, still feeling like she was breathing out a lot more air than she was taking in, and she looked at him, her lip bleeding slightly from where she bit down too hard. "Can I say something now?"_

_He held back a wince at the raspy, deep tone her shouting caused and shrugged. "Yeah, I guess."_

_In a flash she was on top of him, her nails relentlessly digging into the skin of his chest. "My turn."_

* * *

After she finished recalling her dream, they sat in an almost awkward silence. Jack's fingers were placed over his lips as he leaned his elbows on the leg that was crossed over his knee, his eyes intent on her face. Karen cleared her throat again and reached for her martini, downing the rest of it. "So," she shrugged, setting the empty glass back down. "There ya go." There was actually more to her dream, but she had cut it short when she saw his eyes darting around the room and noted the constant shifting in his seat.

Jack sat up, running his hand over his face as he let out a long breath. "Wow."

"Mmm." Karen stared at him, seeing the uneasy look on his face and she sighed, standing up. "This was probably a bad idea, honey," she said. "I'm gonna go home and drink myself to sleep."

"Karen, it's not-" he tried to say as he stood as well, but she grabbed her purse and opened the door anyway. 

"I made you uncomfortable, Jack. It's obvious. Just forget I said anything, okay?" she pleaded, her eyes surprisingly showing more emotion than he was expecting. He agreed and watched her step out of the apartment. "Call me tomorrow, Poodle. We'll go shopping."

Jack waved and closed the door when Karen disappeared in the elevator. He leaned against the wooden door and looked down to the cause of his unease, the bulge in his khaki pants growing even more as he replayed her words in his head. 

 

 


End file.
